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In 2002, the New York Times Magazine began publishing Chris Ware’s serialized comic strip, “Building Stories,” which introduces readers to a three-story row house in the Chicago neighborhood of Humboldt Park. The building is represented as a character that struggles to interpret the motives of a woman who examines it from across the street. Focusing on Humboldt Park, this chapter explores Ware’s concerns about the process of gentrification and the effects it has on Chicago’s architectural and human terrains. It analyzes “Building Stories” in the context of current debates about gentrification in Chicago and other major U.S. cities, arguing that the comic strip is a critique of gentrification and a defense of urban historic preservation. The chapter interprets Ware’s attention to the inner life of the row house as a tribute to historic buildings and an attempt to inculcate in his readers an appreciation for them.